Dimethylformamide → HCID 57756545, compound

HRID 228971Notes

Reaction equation

HRID 228971 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[OH:18])[N:14]=[CH:13][CH:12]=[C:11]2[O:19][C:20]1[C:21]([CH3:30])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.Br[CH2:32][C:33]([NH2:35])=[O:34].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:32][C:33]([NH2:35])=[O:34])[N:14]=[CH:13][CH:12]=[C:11]2[O:19][C:20]1[C:21]([CH3:30])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 1358548286-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol2×

Product 1

HCID 57756545HCID 57756545, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N-Dimethylformamide (1.5 ml) was added to 6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (50 mg), bromoacetamide (62 mg), and potassium carbonate (62 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (49 mg, yield 83%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-5e5fe6665a1a4fd5976565cf63729c4e
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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